While it's very true that the world of Lolita is rot with "laws", "rules" and "guidelines" that some people may find "repressing" It is also a lovely place full of artistic freedom. How is a world both repressing and freeing?
...Allow me to elaborate.
First, let me make a point of the fact that the rules of lolita are not meant to tell you what to wear. But rather, to tell you if what you wear IS lolita. And if these "rules" did not exist, then the beauty and integrity of the fashion would be diminished. For instance, if lolita could be made of any material , if it could be made any length, if it could be less elegant, then would you feel the same way about the fashion? Certainly not. A dress with lace and bows is not necessarily lolita. Take these two picture for example. Both have lace, a gothic lolita color scheme, and full skirts. But these are in no way lolita. Remember, lolita has no rules that say your dress should have lace, bows, frills, etc. So those factors alone are not qualifiers for lolita fashion.
But the "laws" that shape the fashion do not shape the people that wear it. Lolita has so many sub-styles, colors, and themes that almost anyone could find something they like, while still following the guidelines. And many girls find wonderful ways of expressing themselves within this medium. Lolita can very much be a reflection of who you are, if who you are corresponds with the philosophies and ideas that bred this unusual fashion. It's important to remember that even the fashions and time periods that influenced lolita had strict laws about what is and is not acceptable. And, more often than not, the people who like lolita fashion are more than willing to follow it's guidelines, because they can be very helpful for achieving your desired look. In many ways, rules are a lolita's best friend. They make understanding and reaching our doll-like goals much easier. But if you still find the rules too strict, then there are many alternative fashions that will suit your personality. As much as we may not want to believe it, lolita is strict. Some people find that aspect of lolita attractive and interesting, some people like to follow the rules and be part of this fashion. Still, many do not. The important thing to remember is that you should wear what makes you happy. Lolita makes me happy, I'm okay with the rules. But if your not, it isn't the only great style out there. There's something for everyone.
These are only just a few basics to keep in mind:
1.The length of your lolita skirt/dress should be no more than one or two inches above the knee.
2. Fishnets, corsets, and (Please excuse the crude term I'm using for lack of a better word)"stripper boots" don't suit this fashion at all. And can give off a very fetish-like feel.
3.Nothing low-cut should be worn in this fashion. Cleavage doesn't exactly give off that child-like charm we're aiming for.
4.The material commonly used in lolita fashion is cotton. No scratchy or shiny fabric should be used. It can look costume-ish.
5.You shouldn't ever let your petticoat show. It should be one or two inches shorter than your skirt/dress.
6.You MUST wear bloomers. It's not a matter of comfort, but rather a matter of modesty. And is a necessary part of this fashion.
7. It's proper to wear a blouse under your jsk, or a cardigan over it. I've seen lolitas that don't do this, and I doubt that anyone will cut your head off for it. But it always looks a a little better in my mind.
8.While there are set rules on how your dress must not be shorter than 1 or 2 inches above the knee, the rules about how long your dress can be are a little less clear. As far as I can tell, your dress can be up to mid-calve while still maintaining it's childish charm. But when you make it-say around the ankle length, it starts to look like inaccurate Victorian costumes. Also, keep in mind that dresses and skirts that come up to mid-calve can make you look a little shorter, so wearing shoes with a slightly longer heel might counter act that.
9. Though some would argue that as a lolita you do not necessarily need to be proper or even kind, I find the image of an adorable lolita cursing and behaving inappropriately a ghastly sight indeed. No, I should hope that a lolita would take the time to consider the basic rules of manners every person should put to practice. Please remember that as a lolita, you are the face of this fashion. And people will most likely judge it solely on the way you present yourself.
If you'd like a more in-depth look at etiquette and manners, then this fascinating article is a great source of info.